But Harry certainly isn’t the royal to be involved in a controversial romance. It turns out, royal relationship scandals have taken place for years since the 1500s—and they even include a beheading or two.

1. Prince Andrew and Koo Stark

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Harry's uncle Prince Andrew found himself in a similar predicament as his nephew when he dated an American actress in the ‘80s. Her name was Koo Stark, best known for her breakout role in the 1976 erotic film Emily, and she carried on an 18-month long relationship with Queen Elizabeth II’s second son.

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The relationship was heavily criticized because an actress was not seen as the ideal woman for a prince to walk down the aisle with—especially one with a history of risqué movies, Majesty Magazine editor-in-chief Ingrid Seward told Variety.

“In those days, a prince of the realm might have had an actress as a mistress, just like his ancestors would have done, but never a wife,” Seward said.

Seward said Andrew and Stark’s romance ultimately fizzled over media pressures, but the duo are said to remain close friends to this day.

2. Princess Diana and James Gilbey

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Prince Harry’s parents, Princess Diana and Prince Charles, were notorious for their rocky romance. On July 29, 1981, the pair were married in a lavish ceremony that was broadcast around the world, but their love story was anything but a fairytale.

Rumors often swirled of Charles’ infidelities with his now-wife Camilla Parker-Bowles, which Diana openly admitted contributed to her struggles with an eating disorder.

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However, Diana was not completely free of rumors in the relationship. She, too, was caught in a scandal the media titled “Squidgygate” in the early ‘90s, multiple outlets reported.

British intelligence allegedly recorded Diana and her secret lover, James Gilbey, in several phone calls, in which Gilbey said “I love you” and affectionately referred to Diana as “Squidgy” at least 53 times. The tapes were sold to The Sun and later published in The National Enquirer in the U.S. in 1992.

Buckingham Palace never went after the papers for the leak because the royal family did not confirm who was actually on the calls. A 1997 Frontline episode titled “The Princess and the Press” discussed a statement the monarchy issued in which they said they “weren’t taking the tapes seriously.”

Diana and Charles separated in 1992, the same year as the leak, and their divorce was finalized in 1996.

3. Sarah Ferguson and John Bryan

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Although Diana and Charles’ separation in 1992 captivated most audiences, that August, another member of the royal family garnered some negative attention in the media herself.

Sarah Ferguson, Duchess of York, was fresh off her separation from Charles’ brother, Prince Andrew, when photos of her leaked in the press. The pictures, published in The Daily Mirror, appeared to show American businessman John Bryan sucking on Sarah’s toes while she sunbathed topless.

Fergie faced a lot of backlash from the British royals over the embarrassing photo scandal—and in the court of public opinion.

In a poll published in the Sunday Express on August 23, 1992, nine out of 10 people said Ferguson should be stripped of her title if Andrew went through with the divorce.

Richard Kay, a well-known royal writer for the Daily Mail, said he was there on the night Fergie and Bryan learned of the photos, and that Bryan minimized the act as merely “kissing” her feet, not sucking on them.

4. Prince Charles and Camilla Parker-Bowles

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While Sarah Ferguson’s toe-sucking may not be too taboo these days, Prince Charles’ sex talk is most likely not everyone’s cup of tea to this day.

Also in 1992, a private phone conversation between Charles and Camilla Parker-Bowles leaked all over British tabloids after a radio buff accidentally picked up the calls on his high-tech scanning equipment, a 1993 Los Angeles Timesarticle states.

"Oh, God. I'll just live inside your trousers or something. It would be much easier!” Charles can be heard saying in the tapes. "What are you going to turn into, a pair of knickers?" Camilla responds. "Or, God forbid, a Tampax. Just my luck!” he says.

For most, talk of menstruation doesn’t scream romance, and that certainly was the sentiment among many Brits. According to the Sydney Morning Herald, royal biographer Anthony Holden noted that the intercepted phone call ''persuaded most of the nation that the heir to the throne, the would-be Defender of the Faith, was a lavatory-minded adulterer."

The controversy was dubbed “Camillagate” and, because of the timing, seemed to be proof of Charles’ infidelities.

However, because the release of these tapes coincided with those of Diana and James Gilbey, many questioned whether the British internal intelligence was somehow involved. This theory was never confirmed.

5. Princess Diana and James Hewitt

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In a 1995 interview with BBC reporter Martin Bashir, Diana admitted to a love affair with British army officer James Hewitt during her marriage to Prince Charles.

“He was a great friend of mine at a very difficult, yet another difficult time, and he was always there to support me,” Diana said. When Bashir asked if the relationship had gone beyond a close friendship, the princess responded, “Yes it did, yes.”

However, Diana said she felt betrayed by Hewitt, who was heavily sourced in a tell-all about her affairs. In the book, titled Princess in Love, Hewitt said their romance began around 1986, a time in which he said Diana was estranged from her husband. He claimed the relationship started to fade when he was dispatched for duty to Germany in 1989.

When these revelations came to light, many focused on one of Hewitt’s physical attributes in particular: his red hair. Rumors swirled that Hewitt was Harry’s real father, but even Hewitt himself has frequently denied the allegations.

In a TV interview earlier this year with Australian Channel Seven's Sunday Night, the interviewer asked, “Are you Harry’s father?” “No, I am not,” Hewitt responded, adding that the rumor may have lived on for years because it “sells papers.

6. Captain Mark Phillips and Princess Anne

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Princess Anne, the only daughter of Queen Elizabeth II and Prince Phillip, had her fair share of heartbreak in her marriage to Captain Mark Phillips.

The two wed in 1973, and in 1985, Phillips fathered a love child named Felicity with a New Zealand art teacher named Heather Tonkin. A DNA test was conducted as a result of a 1991 paternity suit, confirming that Felicity is Phillips’ daughter, The Telegraph reported.

However, a love child was not the only problem the couple faced. Throughout Anne and Phillips’ marriage, it was widely noted that the pair seemed to lead two separate lives.

A 1989 Peoplestory dubbed them a “loveless duo” and stated that the royal couple lived apart for almost two full years before calling it quits.

They officially divorced in 1992 and Princess Anne got remarried that same year to her current husband, Timothy Laurence.

7. Edward VIII and Wallis Simpson

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In 1936, just months into King Edward VIII’s reign, he proposed to American socialite Wallis Simpson. However, unlike Meghan Markle, it wasn’t Simpson’s nationality that caused a social stir.

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The proposal created a constitutional crisis in the U.K. because, at the time, it was forbidden for the king, who was also the head of the Church of England, to marry a woman who had previously wed and her husband was still alive. Simpson had two living ex-husbands at the time of the proposal.

Meghan Markle, who is also a divorcée, would have shared similar struggles had she and Harry dated during those times. The 36-year-old actress married film producer Trevor Engelson in 2011, but the couple split in 2013.

However, thanks to changes in a religious law in The Church of England, Harry and Markle are free to marry at Westminster Abbey whenever they’d like, Elle UK reports – granted they receive the Queen’s permission, of course.

Unfortunately for Edward, he wasn’t born in Harry’s era and had to choose between the crown and love. He ultimately decided to abdicate the throne and married Simpson in France in 1937, after her second divorce became final.

They later became known as the Duke and Duchess of Windsor.

8. Princess Margaret and Peter Townsend

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Princess Margaret, Queen Elizabeth II’s younger sister, was yet another royal who was met with disapproval when it came to her dating life.

At around 1953, the young princess had to ask her older sister for permission to marry Peter Townsend, a royal equerry who was 16 years her senior.

He had been married before, but divorced his first wife after she allegedly had an affair.

The couple were denied the right to marry multiple times because of Townsend’s divorce, and even Margaret’s title and income were threatened.

Ultimately, she decided to take a different route than Edward VIII and did not pursue a romantic relationship with Townsend.

"I would like it to be known that I have decided not to marry Group Captain Peter Townsend," she said in a public statement. "I have been aware that, subject to my renouncing my rights of succession, it might have been possible for me to contract a civil marriage. But, mindful of the Church's teaching that Christian marriage is indissoluble, and conscious of my duty to the Commonwealth, I have decided to put these considerations before any others."

9. King Henry VIII and his many wives

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King Henry VIII, who ruled England from 1509 to 1547, could have given Elizabeth Taylor a run for her money when it came to multiple marriages.

He was married six times and even had his first marriage to Catherine of Aragon annulled—a controversial move that was frowned upon by the pope at the time.

However, it wasn’t just Henry’s many wives that would have landed him in the tabloids these days, but also the unusual health struggles that many of the women suffered when trying to get pregnant.

His second wife, Anne Boleyn, with whom he cheated on Catherine, suffered a miscarriage in 1534. There is also speculation that she may have had a few stillborn babies prior to that.

Henry reportedly viewed her inability to give him a son as a betrayal. However, this was not the worst of it for Anne. She was later accused of committing several acts of adultery, which led to her execution in 1536.

One day after Anne’s execution, Henry became engaged to Jane Seymour. Four more wives would follow, including Catherine Howard, who was beheaded for adultery

Spousal trouble was an ongoing theme in Henry’s life. Many of his wives suffered reproductive issues, either giving birth to stillborn babies or having children who died shortly after birth. This brought the king’s own health into question.

In The Historical Journal, bioarchaeologist Catrina Banks Whitley and anthropologist Kyra Kramer stated that Henry’s blood group may have been a contributing factor to his many reproductive woes.